


It Looks Better on You

by BasicButler



Category: Critical Role (Web Series)
Genre: Canon Compliant, F/M, Fluff, Widojest - Freeform, i am trash
Language: English
Status: Completed
Published: 2019-07-16
Updated: 2019-07-16
Packaged: 2020-06-29 07:04:39
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,753
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19825009
Author URL: https://archiveofourown.org/users/BasicButler/pseuds/BasicButler
Summary: There are many things that look better on Jester and that is how Caleb knows he wants the world for her. (Basically moments of Caleb being a soft boi and Jester trying to convince him he's a good man).





	It Looks Better on You

**Author's Note:**

> Hi! I don't really write fanfiction, but when I do it's inspired by a rewatch of Campaign 2. Hopefully you don't think this is total garbage, but, let's be honest, it probably is.

“It looks better on you.”

Later that night as Caleb listened to the soft sounds of his companions sleeping, those words replayed in his mind. He said them innocently enough, he supposed. In fact, he’d said them rather thoughtlessly. It was just a fact. After all, pretty much everything would look better on Jester - especially that disgusting pink haversack (he couldn't pinpoint why, exactly, it worked for her). Still, he couldn’t shake the feeling of blood rushing to his ears after he spoke those words. Nor could he shake the image of Jester’s mischief-filled eyes or the lilt of her sweet and teasing voice. His mind was being led to a conclusion Caleb certainly was not equipped to deal with at the moment. 

He sighed softly, turning over and looking at the young Tiefling woman, her brow tightly scrunched together in her sleep. Caleb found himself wanting to banish whatever dream was contorting her face. He knew it was silly, illogical. He also knew that her time spent with the Iron Shepherds would haunt her for a long time. He wished he could have stopped them from taking her at all - if he’d just been slightly more aware she wouldn’t have had to go through that ordeal, her innocence would have been that much more preserved. 

A darker part of him made him think that her experience would be a wake up call for the young Tiefling - this world was a dangerous one and not as filled with fantasy as Jester would like it to be. He was quick to stifle that thought, though, because being tortured shouldn’t be the way anyone discovers how shitty the world is. Especially Jester. Sweet, kind, bright Jester. Still, there was nothing to be done about it. 

Just like there was nothing to be done about Caleb’s affections towards her. He supposed he would just have to be careful about expressing them until they naturally went away. He was attracted to her light, after all, which is hardly all of Jester. He doubted anyone knew who Jester truly is, except, perhaps, the Traveller. But Caleb wasn’t even completely certain the entity was real. 

Huffing out another breath, Caleb dragged his eyes away from Jester back to the night sky, letting his mind wander on the question of the Traveller and finally drifted to sleep. 

*** 

“I think she is faking it,” Caleb observed quietly as him, Fjord, and Beau watched Jester dance on her own at the end of the bar. Both men were already well into their cups and, as conversations usually do when drunk, they turned towards the heavier topics sitting like a fog upon their small, mismatched group. 

Caleb was not ill-equipped to make this observation, he spent a lot of time watching Jester, after all. Especially since recovering her, Fjord, and Yasha from the Iron Shepherds. Often on their trip back to Zadash, Caleb found himself searching for her. The relief that coursed through him when he looked over his shoulder to see the young woman there, safe, if not sound, was, both overwhelming and confounding. 

“Maybe,” Beau acquiesced, no doubt taking in the occasionally odd forced gesture as Jester danced to music only she could hear. 

“I suppose everyone deals with trauma in their own ways,” Fjord took another sip of his drink, unsettled as he saw Jester’s antics from a new angle. 

“I don’t think she’s ever had to deal with it - at least not really,” Caleb noted, “The Traveler has always been beside her from a young age, ya?” 

“You think - what - he’s just some sort of coping mechanism?” 

“No, I think he must be real but, there must have been a reason he came to her like a friend. I will not claim to be an expert on religion but I think most gods do not do that.” 

***

Caleb tossed and turned for an hour before deciding he couldn’t sleep. Instead of staring up at the dark ceiling, though, he decided to make use of his time and, careful not to disturb Nott, found a candle and his writing supplies, before wandering downstairs to work on his spells. 

Under the candlelight, Caleb fell into a familiar rhythm and was able to clear his mind from the worries that had plagued him recently. Study always did that for him. Which is why it is one of his favorite things to do. The others may laugh at him for it, but, as Fjord pointed out earlier, everyone deals with trauma in their own ways and Caleb’s way just happened to be hours of studying or a good book. 

So focused on the spell, Caleb didn’t even notice when a body slid into the space next to him. 

“What are you doing, Caleb?” Came an inquisitive voice that caused Caleb to nearly jump to the ceiling and caused him to splatter ink all over the page. His hand was halfway to his spell component pocket before he was able to settle his heart beat enough to see that it was just Jester. 

“Jester -” Caleb huffed, trying to gloss over his startled reaction, “Do not sneak up on me.” He says perhaps a touch too severely. Jester looked thoroughly rebuffed and Caleb tried to soften his facial expression. Crestfallen did not suit Jester. Jester grabbed one of his quills and, before he could stop her, was writing, ‘I'm very sorry,’ on the corner of the page. 

“It’s fine,” He brushed her small blue hand away from the page and noted the loopy writing and splotches of ink with distaste - the page was beyond saving.

“I just wanted to know what you were doing,” Jester pouted, placing her chin in her hands and looking at Caleb with large, baleful eyes. Caleb looked away before they could cause heat to stir up into his ears and cheeks. 

“I was just studying,” Caleb coughed out.

“But it is so so so late.”

“Ya - I sometimes cannot sleep so I study.” 

“That’s kind of really boring, you know.” 

“Maybe for you, but I like to study.” The Tiefling shrugged her shoulders in an exaggerated motion. Caleb thought it was in a very cute way but, cute is kind of Jester’s area of authority so it was not a surprise. “You like to draw, ya?” Jester nodded enthusiastically. 

“Yea, I like to draw a lot of things, like monsters and unicorns and - 

“Dicks?” Caleb suggested with a slight quirk of his lips. Jester laughed. 

“Yea, especially dicks, they are just so very funny.” 

“Well, drawing is for you like studying is for me.” Caleb explained. 

“Except drawing isn’t boring.” Jester countered matter of factly in a sing song tone. Caleb sighed. 

“Maybe.” 

“Do you want to draw with me?” Jester asked in her very-most-polite tone that had Caleb side eyeing her suspiciously.

“Ya, sure.” Jester brought out her journal and held it close to her until she found two blank pages before she set the journal in front of them. 

“You get this side, and I’ll get this side.” Jester pointed before she grabbed one of his quills and immediately began to draw. Caleb was left a little speechless as he watched the woman focus earnestly on whatever image had struck her fancy. Her teeth bit lightly into her bottom lip and he was sorely tempted to stop the abuse. Still, he turned his attention back to his half of the page. 

Caleb, although creative, was creative in the sense of academia. He liked experiments and figuring things out in newer, better ways. He did not necessarily have the mind for procuring fanciful images. So, without any outside inspiration, Caleb began to draw a render of Jester, her face highlighted by the flickering candle light. Her eyes narrowed in concentration. Her tongue slightly protruding from pearly teeth. Her posture cradled over the journal. 

When he was finished he was satisfied that he’d captured the essence of Jester if not her exact features. And, being so unpracticed, he figured that was enough. Jester was still focused on her work, though. The Tiefling having foiled his every (poorly concealed) attempt to peek at the project, Caleb decided to turn back to studying while he waited for her to unveil her precious creation. 

He studied peacefully for 32 minutes and 45 seconds before Jester waved an excited hand in his face and exclaimed “Done!” 

“Isn’t it perfect Caleb?” Jester asked wistfully while dragging out the ‘a’ in his name as she shoved her side of the journal into his face. The wizard had to lean back to get his eyes to focus. 

“That is a cage, ya?” 

“Yesss,” Jester said, “But all of us are inside it, together.” She motioned her hands in an arc as she said this before entwining her hands; to symbolize ‘togetherness’, Caleb assumed.

“That is kind of dark, Jester,” He paused, eyebrows scrunching together, “and why do we all have penises?” 

“You just don’t know art, Caleb,” Jester sighed exaggeratedly and leaned back. Caleb let out a breath he didn’t realize he’d been holding. 

“Maybe.” Caleb conceded. 

“Your drawing is very beautiful, though,” Jester said, her eyes tracing the angles of her own face with a glimmer of approval that Caleb latched onto. 

“Well of course it is beautiful - it is you.” Jester squealed as Caleb blanched at his own words. She hugged him tightly from where they were seated. 

“Caleb, you are just so so so nice.” As usual in life, Caleb was awkwardly perched between pushing her away and letting himself relax into the hug. He settled for two pats on her side and a pair of burning ears and cheeks. 

“Agree to disagree,” Caleb squeaked out as he pulled himself away, his hands immediately began to entangle themselves together under the table. 

“But you are,” Jester leaned her head on his shoulder, then, even as she felt Caleb thoughts were drifting slightly out of reach. “Thank you Caleb.” She breathed. Caleb thought he understood what it was for well enough. 

“Anytime, Jester,” He replied just as quietly. There was a pause as Caleb adjusted his face so her horn wasn’t nearly poking out his right eye. 

“Did you see that I drew your dick the biggest?” 

“Ya, I noticed.” There was another pause as both of them smiled. Jester’s smile was bright with that ever present glimmer of mischief. Caleb smiled in a distant way, like he was experiencing this moment from a thousand miles away. “Thank you, Jester.” 

“You are very welcome, Caleb.”


End file.
